D-Serine → HCID 24798221, compound

HRID 492063Notes

Reaction equation

[NH2:1][C@@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].[CH3:8][CH:9]([CH3:27])[CH2:10][C:11]([O:13][CH2:14][CH2:15][O:16][C:17](ON1C(=O)CCC1=O)=[O:18])=[O:12]>>[OH:4][CH2:3][C@@H:2]([NH:1][C:17]([O:16][CH2:15][CH2:14][O:13][C:11](=[O:12])[CH2:10][CH:9]([CH3:8])[CH3:27])=[O:18])[C:5]([OH:7])=[O:6]

Participants

Reactant 2

HCID 71077D-Serine

HCID 86618764HCID 86618764, compound

Product 1

HCID 24798221HCID 24798221, compoundYield 59%

Procedure

Following the general procedure for the synthesis of acyloxyalkyl carbamates, D-serine (252 mg, 2.4 mmol) and (2,5-dioxoazolidinyloxycarbonyloxy)ethyl 3-methylbutanoate (574 mg, 2.0 mmol) were reacted to provide 326 mg (59% yield) of the title compound (26) as a white powder after work-up and mass-guided preparative HPLC purification. 1H NMR (CDCl3, 400 MHz): δ=6.80 (m, 1H), 6.11 (m, 1H), 5.78 (br s, 1H), 4.41 (m, 1H), 4.04 (m, 1H), 3.94 (m, 1H), 2.01-2.24 (m, 3H), 1.48 (2d, 3H), 0.99 (2d, 6H). MS (ESI) m/z 278.04 (M+H)+; 295.09 (M+NH4)+; 300.04 (M+Na)+; 276.10 (M−H)−.

Workup

customwere reacted

Sources & evidence

ORD record: ord-4944ed715e24474f92e1349b3f856d24
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531572B2

Reaction notes

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